10.1007/s10593-009-0322-7
The research focuses on the heterocyclization of 2-acetyl-3-indolylacetic acids using hydrazine, with the aim of synthesizing 2,3-dihydro-2-oxo-5-R1-1H-[1,2]diazepino[4,5-b]indoles. The experiments involved various reactants, including 2-acetyl-3-indolylacetic acid derivatives, hydrazine hydrate, and different amines, leading to the formation of compounds such as 2-aminoindolo[2,3-c]pyridin-3(2H)-one and azines. The study also explored the synthesis of these diazepino[4,5-b]indoles through the reaction of 1-alkylaminoacetylindolo[2,3-c]pyrilium perchlorates and methyl esters of 2-acetyl- and 2-propionyl-3-indolylacetic acid with hydrazine hydrate. The analyses used to characterize the synthesized compounds included 1H NMR spectroscopy, mass spectrometry, and X-ray diffraction structural analysis, which provided detailed information on the chemical shifts, molecular structure, and crystallographic data of the compounds.
10.1080/00397911.2019.1681001
The research focuses on the catalyst-free cyclocondensation of β-ethylthio-β-indolyl-α, β-unsaturated ketones with hydrazines, leading to the efficient synthesis of 3-pyrazolyl indoles. This method avoids the use of large excesses of catalysts such as acids and bases, thus reducing the discharge of harmful chemicals and addressing environmental and safety concerns. The reactants used in the study include β-ethylthio-β-indolyl-α, β-unsaturated ketones and hydrazine hydrate. The experiments were optimized to achieve excellent yields under the best conditions, which were found to be a 1:2 molar ratio of ketones to hydrazine, using tert-butyl alcohol as the solvent, and conducting the reaction at 120°C for 4 hours in a sealed tube. The synthesized compounds were characterized using spectral and analytical data, including 1H and 13C NMR spectra recorded on a Bruker DRX-600 spectrometer, HRMS analysis on a Bruck micro Tof using ESI method, and melting points were determined without correction. The reaction products were purified by silica gel column chromatography, and their structures were confirmed with the help of these analyses.
10.1007/s00706-007-0649-7
The research focuses on the synthesis of novel heterocyclic compounds, specifically 1,2,4-triazol-3-ylmethyl-, 1,3,4-oxa-, and -thiadiazol-2-ylmethyl-1H-[1,2,3]-triazolo[4,5-d]pyrimidinediones, which are potentially useful as antiviral agents against hepatitis B virus. The experiments involved the synthesis of 1-carbethoxymethyl-4,6-dimethyl-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione and its subsequent reactions with hydrazine hydrate to yield a hydrazide. This hydrazide was further reacted with phenylisothiocyanate or carbon disulfide and KOH to produce thiosemicarbazide and oxadiazole derivatives. Various alkylation and cyclization reactions were performed to form the desired heterocyclic structures, including the formation of 1,3,4-thiadiazole, 5-mercapto-1,2,4-triazole, and 1,3,4-oxadiazole rings. The synthesized compounds were analyzed using techniques such as infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS) to confirm their structures. The reactants used in these syntheses included phenylisothiocyanate, carbon disulfide, alcoholic potassium hydroxide, dimethyl sulfate, ethyl chloroacetate, and various monosaccharide aldoses. The synthesized compounds were tested for their antiviral activity, with some showing moderate activities against hepatitis B virus.
10.3184/030823408X360355
The research describes a novel and efficient method for the one-pot synthesis of aryl vinyl ethers using β-phenylselenoethanol as a reagent. The purpose of the study was to develop a more experimentally simple and efficient methodology for the preparation of aryl vinyl ethers, which are key intermediates in various synthetic applications and polymeric materials. The researchers achieved this through a two-step process involving the Mitsunobu reaction of β-phenylselenoethanol with phenols, followed by oxidation-elimination with 30% hydrogen peroxide. The method concluded with good yields (85–90%) and had the advantages of mild reaction conditions and convenient manipulation. Key chemicals used in the process included β-phenylselenoethanol, phenols, diphenyl diselenide, sodium hydride, HMPA, 2-chloroethanol, and various phenolic substrates with different substituents. The study also reported the recovery of diphenyl diselenide in a 60% yield through the addition of hydrazine monohydrate to the aqueous extract containing benzeneseleninic acid.
10.1016/j.ejmech.2011.03.028
This research focuses on the efficient microwave-assisted synthesis and antitumor activity evaluation of novel 4,4'-methylenebis[2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)phenols] and methylenebis-2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-4,1-phenylene diacetates. The study aims to develop new bisdiarylpyrazoline derivatives with potential antitumor properties using a high-throughput microwave-assisted synthetic approach. Key chemicals used in the synthesis include salicylaldehyde, substituted acetophenones, hydrazine hydrate, and acetic acid. The microwave-assisted reactions enabled rapid and efficient synthesis of the target compounds. The antitumor activity of selected compounds was tested against 60 different human tumor cell lines, with compounds 4a and 4c showing promising activity, exhibiting GI50 values in the range of 1.75–9.48 μM and LC50 values higher than 100 μM, indicating low toxicity to normal human cell lines. The study concludes that these compounds have significant antitumor potential, with compound 4a being particularly active against leukemia cell lines, making it a promising lead molecule for further development of bispyrazoline derivatives with enhanced antitumor activity.
10.1016/S0022-328X(99)00347-2
The study focuses on the synthesis and characterization of square planar cationic rhodium(I) dicarbonyl complexes with bidentate imidazolyl ligands. The complexes {[Rh((mim)2CO)(CO)2]+BPh4 } (1), {[Rh((mim)2CH2)(CO)2]+BPh4 } (2), and {[Rh((mBnzim)2CH2)(CO)2]+BPh4 } (3) [mim=N-methylimidazol-2-yl, mBnzim=N-methylbenzimidazol-2-yl] were prepared and their structures confirmed as square planar using X-ray crystallography. The carbonyl ligands in complexes 2 and 3 were shown to be labile and could be readily exchanged for triphenylphosphine to form {[Rh((mim)2CH2)(PPh3)2]+BPh4 } (7) and {[Rh((mBnzim)2CH2)(PPh3)2]+BPh4 } (8). The complexes were fully characterized by high-field NMR spectroscopy, and the study also explored the ligand exchange reactions and the structural implications of these exchanges.
10.1007/s00044-013-0887-7
This research presents the synthesis and anticonvulsant evaluation of new 6-bromoimidazo[1,2-a]pyridine-2-carbohydrazide derivatives, which are designed to possess biologically active hydrazone functionality and substituted 1,2,4-triazole moieties. The purpose of the study was to develop novel antiepileptic drugs with improved therapeutic actions and reduced toxicity. The synthesis involved various chemicals such as 5-bromo-2-aminopyridine, ethyl bromopyruvate, hydrazine hydrate, aromatic aldehydes, carbon disulfide, potassium hydroxide, and different alkyl/benzyl halides. The structures of the synthesized compounds were confirmed through spectral techniques like FTIR, 1H NMR, 13C NMR, and mass spectrometry. The in vivo anticonvulsant properties were assessed using maximal electroshock seizure and subcutaneous pentylene tetrazole methods, with toxicity studies performed using the rotarod method. The research concluded that most of the new compounds exhibited significant anticonvulsant properties without toxicity up to 100 mg/kg, with compounds 3b and 4 showing complete protection against seizures, comparable to the standard drug diazepam. These findings suggest that linking imidazo[1,2-a]pyridines with triazole and hydrazone moieties can lead to potent anticonvulsants with minimal side effects.
10.1021/acs.oprd.9b00336
The research focuses on developing a safe and scalable continuous flow methodology for Wolff-Kishner reductions, a chemical process used to convert aldehydes and ketones into alkanes by deoxygenation. The purpose of this study was to address the safety and scalability concerns associated with the traditional batch process, which involves the use of hazardous hydrazine hydrate and caustic bases under harsh conditions. The chemicals used in the process include α-tetralone, NaOH, N2H4?H2O (hydrazine hydrate), and methanol.
10.1007/s00044-011-9921-9
The study explores the synthesis and pharmacological properties of a series of compounds derived from sydnones. The researchers transformed sydnones into 1,3,4-oxadiazolin-2-one intermediates using bromine in acetic anhydride, and subsequently converted these intermediates into 1,2,4-triazoles by reacting them with hydrazine hydrate. The synthesized compounds were characterized using IR, 1H NMR, MS, and elemental analysis. These compounds were then evaluated for their potential as antihyperglycemic agents, antioxidants, and their ability to induce DNA cleavage. The study found that certain compounds exhibited strong inhibitory activity against α-amylase, indicating potential antihyperglycemic effects, while others showed significant antioxidant and DNA cleavage activities. The compounds were also analyzed for drug likeliness and drug score, with results suggesting they have favorable properties for further development as potential therapeutic agents.
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